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Ethyl nitrite

Ethyl nitrite structure

Ethyl nitrite 

structure
  • CAS No:

    109-95-5

  • Formula:

    C2H5NO2

  • Chemical Name:

    Ethyl nitrite

  • Synonyms:

    Nitrous acid,ethyl ester;Ethyl nitrite;Nitrosyl ethoxide;Nitrous ether;Nitrous ethyl ether;Spirit of ethyl nitrite;Sweet spirit of niter;8013-58-9

  • Categories:

    Organic Chemistry  >  Inorganic Acid Esters

Description

Liquid


Ethyl nitrite, solution appears as a clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31°F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.|Liquid


Ethyl nitrite, solution appears as a clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31°F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.|Ethyl nitrite is a nitroso compound.

Ethyl nitrite Basic Attributes

75.07

75.07

203-722-6

8C7CJ279RV

1194

DTXSID9046574

Colorless or yellowish, clear liquid

2920909090

Characteristics

38.7

0.70430

Ethyl nitrite, solution appears as a clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31°F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.

0.90 g/cm3 @ Temp: 15 °C

FP: -58 deg F= -50 deg C= 233 deg K

17 °C

59 °F

n20/D 1.36

Slightly soluble in water; decomposes in water; miscible with alcohol, ether

Refrigerator

2.6

Inhalation-Rabbit LC50: 160 PPM/ 4 hours

It is flammable in case of open flame, high temperature and oxidant; it produces toxic nitrogen oxide fumes during combustion; it produces toxic nitrogen oxide gas in the presence of acid

3.01% TO 50% BY VOL IN AIR.

SWEET, RUM-LIKE ODOR

FRUITY TASTE

7.00e-13 cm3/molecule*sec

Decomp in water; decomp spontaneously at 194 °F (90 °C)|VERY MOBILE; FORMS AZEOTROPIC MIXTURE WITH ISOPENTANE (85%), AMYL BROMIDE (40%) & CARBON DISULFIDE (96%)|FLOATS ON WATER; MAY BOIL ON WATER; LIQ-WATER INTERFACIAL TENSION: 35 DYNES/CM= 0.035 N/M @ 20 °C|Hydroxyl radical rate constant = 1.75X10-12 cu-cm/molc sec @ 25 °C|Decomposes readily to form oxides of nitrogen.

Highly flammable. Vapors may ignite spontaneously and the reaction may reach explosive violence. Insoluble in water. Decomposes in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Explosive

ETHYL NITRITE is a powerful oxidizing agent. Highly dangerous in contact with acid or acid fumes. Dangerous when heated. Decomposes spontaneously at 194°F. Decomposed by light.

194 °F (USCG, 1999)|194 °F (DECOMPOSES).

-7,800 BTU/LB= -4,300 CAL/G= -180X10+5 J/KG

LOWER, 4.0%; UPPER, 50.0% BY VOLUME IN AIR.

229 BTU/LB= 127 CAL/G= 5.32X10+5 J/KG

Safety Information

I

3.1

UN 1194 3/PG 1

11-20/21/22-2

7-16-35

RA0810000

F,Xn,E

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Thermal explosion

ON KEEPING, IT GRADUALLY DECOMPOSES, BECOMING ACID & OXIDES OF NITROGEN FORM. DECOMP IS HASTENED BY AIR, LIGHT, & MOISTURE.

P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

H225-H319

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

DISASTER HAZARD: HIGHLY DANGEROUS; WHEN HEATED TO DECOMPOSITION OR ON CONTACT WITH ACID OR ACID FUMES, EMITS HIGHLY TOXIC FUMES OF NO(X)...

Ethyl nitrite is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Special Hazards of Combustion Products: Toxic oxides of nitrogen are generated. Behavior in Fire: Vapors are heavier than air and may travel a considerable distance to a source of ignition and flash back; can decompose violently above 194°F; containers may explode in a fire. (USCG, 1999)|Flammable - 4th degree, Reactive - 4th degree

|Danger|H220: Extremely flammable gas [Danger Flammable gases]|P210, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P377, P381, P403, and P501|H220 (100%): Extremely flammable gas [Danger Flammable gases]|P210, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P377, P381, P403, P410+P403, and P501|Aggregated GHS information provided by 271 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. SMALL SPILL: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Self-contained breathing apparatus; goggles or face shield; rubber gloves. (USCG, 1999)|SELF-CONTAINED BREATHING APPARATUS; GOGGLES, OR FACE SHIELD; RUBBER GLOVES.

Flammable liquid.

3.01% TO 50% BY VOL IN AIR.

Use water spray, dry chemical, foam, or carbon dioxide. Use water spry to keep fire-exposed containers cool. Fight fire from protected location or maximum possible distance.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.|Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-half (1/2) mile radius.

Closed containers may rupture violently when heated.

Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.|If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Ethyl nitrite, solution/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Ethyl nitrite, solution/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Ethyl nitrite, solution/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Ethyl nitrite, solution/|For more DOT Emergency Guidelines (Complete) data for ETHYL NITRITE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

CONTACT WITH LIQUID IRRITATES EYES & SKIN.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 4 - Materials that rapidly or completely vaporize at atmospheric pressure and normal ambient temperature or that are readily dispersed in air and burn readily.| 4 - Materials that in themselves are readily capable of detonation or explosive decomposition or explosive reaction at normal temperatures and pressures.

ETHYL NITRITE IS DETECTED IN EXHAUSTS WHEN METHANOL & ETHANOL ARE USED AS FUELS. ETHYL NITRITE CONTENT OF EXHAUST FROM A VEHICLE FUELED WITH ETHANOL & OPERATED AT HIGHWAY CONDITIONS IS 1.0-9.0 & 16.5-27.0 PPM, RESPECTIVELY, IN INITIAL 1/2 HR & IN 17 HR.

Toxicity

highly toxic

LD50 Rat inhalation 160 ppm/4 hr

Ethyl nitrite's production and use for preparing spirit nitrous ether(1), in exhaust from alcohol-fueled vehicles(2), and also for use in organic reactions(3) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that ethyl nitrite is expected to have very high mobility in soil(SRC). Volatilization of ethyl nitrite from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethyl nitrite from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 620 mm Hg(SRC), determined from a fragment constant method(4). A decomposition rate has not been published, however it is known that ethyl nitrite is slightly soluble(5) and decomposes in water(5). In addition, decomposition of ethyl nitrite is hastened by air, light, and moisture(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that ethyl nitrite is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 and 146, respectively(SRC). A decomposition rate has not been published, however it is known that ethyl nitrite is slighlty soluable in water and is decomposed by it(7). In addition, decomposition of ethyl nitrite is hastened by air, light, and moisture(7). According to a classification scheme(5), an estimated BCF of 2(SRC), from an estimated log Kow(8) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: A decomposition rate has not been published, however it is known that decomposition of ethyl nitrite is hastened by air, light,and moisture(4). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl nitrite, which has an estimated vapor pressure of 620 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Vapor-phase ethyl nitrite is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 34.5 days(SRC), calculated from its rate constant of 1.75X10-12 cu cm/molecule-sec at 25 °C(3).

A decomposition rate has not been published, however it is known that ethyl nitrite is slighlty soluable in water and is decomposed by it(2). In addition, decomposition of ethyl nitrite is hastened by air, light,and moisture(2). The rate constant for the vapor-phase reaction of ethyl nitrite with photochemically-produced hydroxyl radicals is 1.75X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 34 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

An estimated BCF of 2 was calculated for ethyl nitrite(SRC), using an estimated log Kow of 1.4(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethyl nitrite can be estimated to be 81(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl nitrite is expected to have high mobility in soil.

The Henry's Law constant for ethyl nitrite is estimated as 8.7X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl nitrite is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 6 days(SRC). Ethyl nitrite's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of ethyl nitrite from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 620 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to ethyl nitrite may occur through inhalation and dermal contact with this compound at workplaces where ethyl nitrite is produced or used. The general population may be exposed to ethyl nitrite via inhalation of auto exhaust from alcohol-fueled vehicles and ingestion of food in which ethyl nitrite has been used as a synthetic flavoring. (SRC)

Drug Information

THE REACTIONS OF HUMAN HEMOGLOBIN WITH SODIUM NITRITE AND ETHYL NITRITE IN DEOXYGENATED MEDIA HAVE BEEN EXAMINED IN KINETIC DETAIL. ETHYL NITRITE REACTS WITH HEMOGLOBIN AT RATES THAT ARE AT LEAST 10 TIMES SLOWER THAN THOSE EXTRAPOLATED FOR NITROUS ACID, & HYDROLYSIS OF ALKYL NITRITE IS NOT COMPETITIVE WITH OXIDATION OF HEMOGLOBIN. THE EXPERIMENTAL RESULTS ARE INTERPRETED TO DESCRIBE ALKYL NITRITE, AND PRESUMABLY, NITROUS ACID ASSOCIATION WITH HEMOGLOBIN FOLLOWED BY RATE-LIMITED ELECTRON TRANSFER RESULTING IN NITRIC OXIDE AND ALKOXIDE (OR HYDROXIDE) PRODN. PROTON TRANSFER RESULTING IN ALC (OR WATER) FORMATION OCCURS SUBSEQUENT TO THE RATE-LIMITING STEP AS DO REACTIONS OF HEMOGLOBIN WITH NITRIC OXIDE.|THE REACTION OF HUMAN HEMOGLOBIN AND SPERM WHALE MYOGLOBIN UNDER AEROBIC CONDITIONS WITH ETHYL NITRITE HAVE BEEN EXAMINED. ETHYL NITRITE CONVERTS TWO EQUIVALENTS OF OXYHEMOGLOBIN TO THEIR OXIDIZED COUNTERPARTS WITH CONCURRENT PRODN OF ONE EQUIVALENT OF MOLECULAR OXYGEN, NITRATE ION, & ETHYL ALCOHOL.

Inhalation or ingestion causes headache, increased pulse rate, decreased blood pressure, and unconsciousness. Contact with liquid irritates eyes and skin. (USCG, 1999)

INHALATION: remove victim from exposure; if breathing has stopped, give artificial respiration; call physician. EYES: flush with water for at least 15 min.; get medical attention if irritation persists. SKIN: flush with water, wash with soap and water. INGESTION: do NOT induce vomiting; call physician. (USCG, 1999)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 l/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat as necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does drool. Administer activated charcoal ... . /Nitrates, nitrites, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Nitrates, nitrites, and related compounds/

MAY CAUSE METHEMOGLOBINEMIA & HYPOTENSION, &, IN HIGH CONCN.../SRP: CNS DEPRESSION/.|Industrial intoxications characterized by headache, tachycardia, and methemoglobinemia have occurred. A fatality has been described following the inhalation of ethyl nitrite after accidental breakage of a 4 liter bottle containing 24% ethyl nitrite in alcohol.|Three cases of ethyl nitrite intoxication have been reported from Czechoslovakia during a synthesis of hydantoin (glycolylurea). Symptoms of both "nitrite" effect and methemoglobinemia were noted. In addition, there was a vasodilator effect upon the blood vessels of the sclerae, producing a peculiar redness of the eyes, ... No Heinz bodies were seen.|ADMIN OF SWEET SPIRITS OF NITRE (4% ETHYL NITRITE IN 70% ETHANOL) WAS FOLLOWED BY ACUTE METHEMOGLOBINEMIA & SEVERE ANOXIC METABOLIC ACIDOSIS IN INFANT TWINS, METHYLENE BLUE ADMIN REVERSED METHEMOGLOBINEMIA IN BOTH, BUT ONE TWIN DIED FROM THE CONSEQUENCES OF HYPOXEMIA.|For more Human Toxicity Excerpts (Complete) data for ETHYL NITRITE (6 total), please visit the HSDB record page.

ethyl nitrite

Ethyl nitrite Use and Manufacturing

Methods of Manufacturing

Sodium nitrite is replaced with sulfuric acid in an aqueous solution to form an acid, and then esterified with ethanol present in the solution.

Uses

This product is an intermediate of pharmaceutical chlorphosphoridine.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Article of commerce contains 90-95% ethyl nitrite, remainder is chiefly alcohol as preservative.

Nitrous acid, ethyl ester: ACTIVE|FEMA LIST OF GRAS SUBSTANCES REPORT USAGE AS SYNTHETIC FLAVOR INGREDIENT IN NON-ALCOHOLIC BEVERAGES 3.0 PPM, ICE CREAM, ICES...4.5 PPM; CANDY 0.10-8.0 PPM; BAKED GOODS 0.10 PPM; CHEWING GUM 3.9 PPM; SYRUPS 52 PPM; ICINGS 13 PPM.|FEMA NUMBER 2446|In prepn of spirit nitrous ether by mixing with 21 parts alcohol by weight.

GAS CHROMATOGRAPHY-MASS SPECTROMETRY DEMONSTRATES PRESENCE OF ETHYL NITRITE IN BREATH OF VOLUNTEER SUBJECTS WHO SMOKE & DRINK CONCURRENTLY. THE MUTAGENIC COMPD IS QUANTIFIED AT THE PPB LEVEL BY GAS CHROMATOGRAPHY.

Fire Hazards -> Flammable - 4th degree, Reactive - 4th degree

Computed Properties

Molecular Weight:75.07
XLogP3:0.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:75.032028402
Monoisotopic Mass:75.032028402
Topological Polar Surface Area:38.7
Heavy Atom Count:5
Complexity:28.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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    Unit Price: $100 /MT FOB
    CAS No.: 109-95-5
    Grade: Pharmacy Grade
    Content: 98.5%
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