Description Uses References
ChemicalBook > CAS DataBase List > 1,2-Dimethoxybenzene

1,2-Dimethoxybenzene

Description Uses References
Product Name
1,2-Dimethoxybenzene
CAS No.
91-16-7
Chemical Name
1,2-Dimethoxybenzene
Synonyms
VERATROLE;Benzene, 1,2-dimethoxy-;VERATROL;Veretrole;ODMB;Synthol;O-DIMETHOXYBENZENE;1,2-Dimethoxybenzol;GUAIACOL METHYL ETHER;CATECHOL DIMETHYL ETHER
CBNumber
CB5144392
Molecular Formula
C8H10O2
Formula Weight
138.16
MOL File
91-16-7.mol
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1,2-Dimethoxybenzene Property

Melting point:
15 °C(lit.)
Boiling point:
206-207 °C(lit.)
Density 
1.084 g/mL at 25 °C(lit.)
vapor pressure 
0.63 hPa (25 °C)
FEMA 
3799 | 1,2-DIMETHOXYBENZENE
refractive index 
n20/D 1.533(lit.)
Flash point:
189 °F
storage temp. 
Store below +30°C.
solubility 
6.69g/l insoluble
form 
Powder
color 
White to cream
Odor
at 1.00 % in dipropylene glycol. sweet creamy vanilla phenolic musty
Odor Type
vanilla
Water Solubility 
Soluble in alcohol, diethyl ether, acetone, and methanol. Slightly soluble in water.
FreezingPoint 
21.0 to 23.0 ℃
Merck 
14,9956
JECFA Number
1248
BRN 
1364621
Dielectric constant
4.0899999999999999
InChIKey
ABDKAPXRBAPSQN-UHFFFAOYSA-N
LogP
1.75-2.22 at 25℃
CAS DataBase Reference
91-16-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, 1,2-dimethoxy-(91-16-7)
EPA Substance Registry System
Veratrole (91-16-7)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-20/21/22
Safety Statements 
36-23-24/25
WGK Germany 
1
RTECS 
CZ6475000
TSCA 
Yes
HS Code 
29093090
Toxicity
LD50 in rats, mice (mg/kg): 1360, 2020 orally (Jenner)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.08529
Product name
Pyrocatechol dimethyl ether
Purity
for synthesis
Packaging
250ML
Price
$55.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.08529
Product name
Pyrocatechol dimethyl ether
Purity
for synthesis
Packaging
1L
Price
$145
Updated
2024/03/01
Sigma-Aldrich
Product number
140155
Product name
1,2-Dimethoxybenzene
Purity
ReagentPlus , 99%
Packaging
100g
Price
$30.1
Updated
2024/03/01
Sigma-Aldrich
Product number
140155
Product name
1,2-Dimethoxybenzene
Purity
ReagentPlus , 99%
Packaging
1kg
Price
$198
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2469
Product name
Guaiacol Impurity C
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
100MG
Price
$466
Updated
2022/05/15
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1,2-Dimethoxybenzene Chemical Properties,Usage,Production

Description

1, 2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is a colorless liquid with a pleasant odor and slight solubility in water.
It is the dimethyl ether derived from pyrocatechol, too.
1, 2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase.1, 2-Dimethoxybenzene is an insect attractant.
Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.

Uses

1, 2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution. An example of the use of veratrole is in the synthesis of Domipizone.
Veratrole can easily be brominated with NBS to give 4-bromoveratrole.

References

1.https://en.wikipedia.org/wiki/1,2-Dimethoxybenzene
2.https://pubchem.ncbi.nlm.nih.gov/compound/1_2-Dimethoxybenzene#section=Chemical-and-Physical-Properties

Chemical Properties

Colorless crystals or liquid. Soluble in alcohol and ether; slightly soluble in water.

Occurrence

Reported present in asparagus (raw and cooked), bonito (dried), broccoli (cooked), cauliflower (cooked), cognac, endive, grape, Gruyere de Comte cheese, guava, leek (raw and heated), olive, peas, rhubarb, rice bran and vanilla extract.

Uses

1,2-Dimethoxybenzene was used to investigate the electroantennogram response of vine weevil, Otiorhynchus sulcatus to plant volatiles.

Uses

Veratrole is common reagent in organic synthesis such as the synthesis of arizonins B1 and C1. Also used in the synthesis of pharmacophores of salmeterol and roflumilast as dual β2-adrenoreceptor agonists-PDE4 inhibitors.

Definition

ChEBI: A dimethoxybenzene with the methoxy groups at ortho-positions.

Preparation

Prepared by methylation of pyrocatechol.
1,2-Dimethoxybenzene can also be prepared from Catechol. The specific synthesis steps are as follows:
 Aqueous sodium hydroxide(40%,175 ml)is added dropwise during 3 hr at 18-22 to a well stirred mixture of catechol (50 g,0.45 mole),sodium hydrosulphite (20 g,0.115 mole),dimethyl sulphate (110 ml,146.63 g, 1.16 mole)and alcohol (150 ml).Ice (1 kg)is added to the reaction mixture and left overnight at room temperature.It is extracted with ether (2x 200 ml).The ether extract is washed with water,dried (anhydrous sodium sulphtate)and distilled.Veratrole is obtained as oil.Yield 52.75 g (84.1%).B.p.207°(1it.3b.p.207).

Taste threshold values

Intolerable at 40 ppm.

General Description

1,2-Dimethoxybenzene reacts with Li{N(SO2CF3)2} to yield molecular crystal [Li{N(SO2CF3)2}{C6H4(OCH3)2}2] having solid-state lithium ion conductivity. It is a potential pollinator attractant of the nocturnal moth Hadena bicruris.

Toxicology

Data from 1,2-dimethoxybenzene and read-across analog 1,4-dimethoxybenzene (CAS # 150-78-7) show that 1,2-dimethoxybenzene is not expected to be genotoxic. Data show that there are no safety concerns for 1,2-dimethoxybenzene for skin sensitization under the current declared levels of use. The repeated dose, reproductive, and local respiratory toxicity endpoints were evaluated using the TTC for a Cramer Class I material, and the exposure to 1,2-dimethoxybenzene is below the TTC (0.03 mg/kg/day, 0.03 mg/kg/day, and 1.4 mg/day, respectively). The phototoxicity/photoallergenicity endpoints were evaluated based on UV spectra; 1,2-dimethoxybenzene is not expected to be phototoxic/photoallergenic. For the environmental endpoints, 1,2-dimethoxybenzene is not a PBT as per the IFRA Environmental Standards, and its risk quotients (i.e., PEC/PNEC) for the aquatic environment, based on its current volume of use in Europe and North America, are < 1

Purification Methods

Steam distil veratrole, then fractionally distil it from BaO, CaH2 or Na. Crystallise it from *benzene or low-boiling pet ether at 0o. Fractionally crystallise it from its melt. Store it over anhydrous Na2SO4. [Beilstein 6 IV 5564.]

1,2-Dimethoxybenzene Preparation Products And Raw materials

Raw materials

Guaiacol Catechol PETROLEUM ETHER Chloromethane

Preparation Products

5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 4-Chloro-3',4'-dimethoxybenzophenone (3,4-Dimethoxyphenyl)acetonitrile 6,7-DIMETHOXY-3-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE 2,3-Dimethoxyphenylboronic acid 3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile
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View Lastest Price from 1,2-Dimethoxybenzene manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
1, 2-Dimethoxybenzene 91-16-7
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-09
WUHAN FORTUNA CHEMICAL CO., LTD
Product
1,2-Dimethoxybenzene 91-16-7
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-02-02
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
1,2-Dimethoxybenzene 91-16-7
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-21

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