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77-78-1

Basic Information
CAS No.: 77-78-1
Name: Dimethyl sulfate
Article Data: 54
Molecular Structure:
Molecular Structure of 77-78-1 (Dimethyl sulfate)
Formula: C2H6O4S
Molecular Weight: 126.133
Synonyms: Dimethyl sulphate;Methyl sulfate;NSC 56194;
EINECS: 201-058-1
Density: 1.323 g/cm3
Melting Point: -32 °C
Boiling Point: 187.999 °C at 760 mmHg
Flash Point: 83.333 °C
Solubility: 2.8 g/100 mL (18 ºC)
Appearance: colourless liquid
Hazard Symbols: VeryT+
Risk Codes: 45-25-26-34-43-68
Safety: 53-45
Transport Information: UN 1595 6.1/PG 1
PSA: 60.98000
LogP: 0.60480
Synthetic route
121-45-9

phosphorous acid trimethyl ester

A

512-56-1

trimethyl phosphite

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -50℃;A 7%
B 93%
67-56-1

methanol

7,12-epoxy-5,6,6a,7,12,12a-hexahydro-2-methoxybenz[a]anthracen-5-one

A

1350749-76-6

2,5-dimethoxybenz[a]anthracene

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfuric acid for 18h; Reflux; Inert atmosphere;A 88%
B n/a
121-45-9

phosphorous acid trimethyl ester

A

512-56-1

trimethyl phosphite

B

152-18-1

O,O,O-trimethylthiophosphate

C

77-78-1

dimethyl sulfate

D

756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -78℃; Product distribution; other trialkyl phosphite,trialkyl phosphine, trialkyl arsines, trialkoxyarsines, var. molar ratio and temperatures;A 22%
B 4%
C 55%
D 19%
With sulfur trioxide In dichloromethane at -78℃;A 48%
B 16%
C 3%
D 9%
6596-95-8

trimethylarsenite

A

80398-42-1

dimethoxyarsenic methyl sulfate

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -50℃;A 39%
B 27%
6596-95-8

trimethylarsenite

A

80398-43-2

methoxyarsenic bis(methyl sulfate)

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -50℃;A 28%
B 38%
6596-95-8

trimethylarsenite

A

80398-44-3

arsenic tris(methyl sulfate)

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -50℃;A 19%
B 21%
149-73-5

trimethyl orthoformate

A

107-31-3

Methyl formate

B

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With sulfuric acid Etherification; Heating;A n/a
B 10%
77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With diethyl ether; sulfuric acid
67-56-1

methanol

812-01-1

methyl chlorosulfate

A

74-87-3

methylene chloride

B

75-93-4

methyl bisulfate

C

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
at -15 - -10℃; und folgenden Destillieren unter vermindertem Druck;
67-56-1

methanol

77-78-1

dimethyl sulfate

Conditions
ConditionsYield
With chlorosulfonic acid at -15 - -10℃;
With sulfuric acid bei der Destillation;
With sulfuric acid anschliessend man destilliert das Reaktionsgemisch im Vakuum;
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  • Casno:

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History

DIMETHYL SULFATE(77-78-1) was first discovered in the early 1800s in an impure form. P. Claesson later extensively studied its preparation.

Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 200.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 , 1974,p. 271.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 , 1974,p. 271.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 0.1 ppm (skin)
ACGIH TLV: TWA 0.1 ppm (skin); Animal Carcinogen
DFG MAK: DFG TRK: Production: 0.02 ppm; Use: 0.04 ppm; Animal Carcinogen, Suspected Human Carcinogen
DOT Classification:  3; Label: Poison, Corrosive

Analytical Methods

For occupational chemical analysis use NIOSH: Dimethyl Sulfate, 2524.

Specification

The IUPAC name of this chemical is Dimethyl sulfate. With the CAS registry number 77-78-1 and EINECS registry number 201-058-1, it is also named as Sulfuricacid, dimethyl ester. In addition, the molecular formula is C2H6O4S and the molecular weight is 126.13. It is a kind of colourless liquid and belongs to the class of Pharmaceutical Intermediates.

Physical properties about this chemical are: (1)ACD/LogP: 0.12; (2)ACD/LogD (pH 5.5): 0.121; (3)ACD/LogD (pH 7.4): 0.121; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 27.723; (7)ACD/KOC (pH 7.4): 27.723; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 60.98 Å2; (11)Index of Refraction: 1.41; (12)Molar Refractivity: 23.597 cm3; (13)Molar Volume: 95.306 cm3; (14)Polarizability: 9.355 ×10-24cm3; (15)Surface Tension: 36.492 dyne/cm; (16)Density: 1.323 g/cm3; (17)Flash Point: 83.333 °C; (18)Enthalpy of Vaporization: 40.684 kJ/mol; (19)Boiling Point: 187.999 °C at 760 mmHg; (20)Vapour Pressure: 0.845 mmHg at 25°C.

Preparation of Dimethyl sulfate: it can be prepared by methanol with sulfuric acid. The methanol react with sulfuric acid to give methyl hydrogen sulfate at first. Then the methyl hydrogen sulfate can react with methanol to get dimethyl ether. At last, dimethyl ether react with sulfur trioxide to prepare the product.

Dimethyl sulfate can be prepared by methanol with sulfuric acid

Uses of Dimethyl sulfate: it can be used as a reagent for the methylation of phenols, amines, and thiols. And it can effect the base-specific cleavage of guanine in DNA by rupturing the imidazole rings present in guanine. This process can be used to determine base sequencing, cleavage on the DNA chain, and other applications. In addition, it can react with 1H-benzoimidazole to get 1-methyl-1H-benzoimidazole. This reaction will need reagents K2CO3 and triethylbenzylammonium chloride and solvent benzene. The reaction time is 0.5 hour at reaction temperature of 20 °C. The yield is about 50%.

Dimethyl sulfate can react with 1H-benzoimidazole to get 1-methyl-1H-benzoimidazole

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed and very toxic by inhalation. And it can cause burns and may cause sensitization by skin contact. Moreover, it may cause cancer and has risk of irreversible effects possibly. You should avoid exposure - obtain special instruction before use. During using it, in case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: COS(=O)(=O)OC
(2)InChI: InChI=1/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3
(3)InChIKey: VAYGXNSJCAHWJZ-UHFFFAOYAK

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC50 inhalation 32ppm/1H (32ppm)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1079, 1986.
human LCLo inhalation 97ppm/10M (97ppm)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 226, 1969.
mouse LC50 inhalation 280mg/m3 (280mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(3), Pg. 28, 1979.
mouse LD50 oral 140mg/kg (140mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(3), Pg. 28, 1979.
rabbit LDLo intravenous 50mg/kg (50mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 47, Pg. 113, 1902.
rabbit LDLo oral 45mg/kg (45mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL) Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 47, Pg. 113, 1902.
rabbit LDLo subcutaneous 53mg/kg (53mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 47, Pg. 113, 1902.
rat LC50 inhalation 45mg/m3/4H (45mg/m3) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: HEMORRHAGE
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(11), Pg. 55, 1980.
rat LD50 oral 205mg/kg (205mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(3), Pg. 28, 1979.
rat LD50 subcutaneous 100mg/kg (100mg/kg)   Zeitschrift fuer Krebsforschung. Vol. 74, Pg. 241, 1970.