5221-17-0

Basic information

• Product Name: 3,5-DI-T-BUTYL-4-METHOXYBENZALDEHYDE
• Synonyms: 3,5-DI-T-BUTYL-4-METHOXYBENZALDEHYDE;2,3-Dibromopropanal;Acrolein Dibromide;Dibromopropionaldehyde;Propanal, 2,3-dibromo-;2,3-dibromopropionaldehyde;2,3-dibromo-propana;2,3-dibromo-propionaldehyd
• CAS NO: 5221-17-0
• Molecular Formula: C₃H₄Br₂O
• Molecular Weight: 248.36
• EINECS: 226-017-5
• Product Categories: Pharmaceutical Intermediates
• Mol File: 5221-17-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 153.1°C (rough estimate)
• Flash Point: 88°C
• Appearance: /
• Density: 2.1920
• Vapor Pressure: 0.502mmHg at 25°C
• Refractive Index: 1.5082 (estimate)
• CAS DataBase Reference: 3,5-DI-T-BUTYL-4-METHOXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DI-T-BUTYL-4-METHOXYBENZALDEHYDE(5221-17-0)
• EPA Substance Registry System: 3,5-DI-T-BUTYL-4-METHOXYBENZALDEHYDE(5221-17-0)

Safety Data

• Hazardous Substances Data: 5221-17-0(Hazardous Substances Data)

Usage

General Description

3,5-Di-T-Butyl-4-Methoxybenzaldehyde is a chemical compound that is often used in various industrial applications. It is generally known for its use in the perfumery and fragrance industries where it is used for its strong, spicy, and vanilla-like scent. The compound has two tert-butyl groups at its 3 and 5 positions, a methoxy group at the 4 position, and it features a formyl (aldehyde) functional group, making it a derivative of benzaldehyde. This chemical should be handled with care as it could cause irritation when it comes into contact with the skin or eyes. The compound is typically synthesized through a complex lab process and should be handled by trained professionals.

InChI:InChI=1/C3H4Br2O/c4-1-3(5)2-6/h2-3H,1H2/t3-/m1/s1

Synthetic route

acrolein (107-02-8) → 2,3-dibromopropanal (5221-17-0)

Conditions	Yield
With bromine In tetrachloromethane at 0℃; Cooling with ice;	80%
With bromine Ambient temperature; competitive bromination with 1-heptene; other unsaturated carbonyl compound;
With bromine

2,3-dibromo-propionyl chloride (18791-02-1) → 2,3-dibromopropanal (5221-17-0)

Conditions	Yield
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran Reduction;	79%

3,4-dibromo-1-butene (10463-48-6) → formaldehyd (50-00-0) + 2,3-dibromopropanal (5221-17-0)

Conditions	Yield
bei der Ozonspaltung;

1,3-dibromo-propane (109-64-8) → 2,3-dibromopropanal (5221-17-0)

Conditions	Yield
With water; bromine

acrolein (107-02-8) → 2,3-dibromopropanal (5221-17-0) + 2,3,3-tribromo-propionaldehyde

Conditions	Yield
With bromine

1,3-dibromopropene (627-15-6) + aqueous bromine → 2,3-dibromopropanal (5221-17-0)

4,5-dibromo-pent-2-enoic acid (85858-56-6) + chloroform (67-66-3) + water (7732-18-5) + ozone (10028-15-6) → 2,3-dibromopropanal (5221-17-0) + oxasoic acid

2,3-dibromopropanal (5221-17-0) + N-(1-trifluoromethyltrifluoroethylidene)-2-trifluoromethyl-3,3,3-trifluoropropionamide (35933-97-2) → 2-(1,2-dibromoethyl)-4,4-bis(trifluoromethyl)-6-(2-hydrohexafluoroisopropyl)-2H,4H-1,3,5-dioxazine (83926-93-6)

Conditions	Yield
In tetrachloromethane at 100℃; for 1h;	94.8%

2,3-dibromopropanal (5221-17-0) + meso-2,3-Dimercaptobernsteinsaeure-dimethylester (17660-57-0) → (4R,5S)-2-(1,2-Dibromo-ethyl)-[1,3]dithiolane-4,5-dicarboxylic acid dimethyl ester

Conditions	Yield
With toluene-4-sulfonic acid	90%

2,3-dibromopropanal (5221-17-0) + sodium benzenesulfonate (873-55-2) → (E)-3-(phenylsulfonyl)acrylaldehyde

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 20h;	76%

2,3-dibromopropanal (5221-17-0) + trimethyleneglycol (504-63-2) → 2-(1,2-dibromoethyl)-1,3-dioxane (89791-57-1)

Conditions	Yield
With cationite KU-2-8 In benzene Heating;	71%
With potassium carbonate; toluene-4-sulfonic acid 1.0 CH2Cl2, reflux, 5 h, 2.) heating.; Multistep reaction;

2,3-dibromopropanal (5221-17-0) + ethylene glycol (107-21-1) → 2-(1',2'-dibromoethyl)-1,3-dioxolane (5267-72-1)

Conditions	Yield
With cationite KU-2-8 In benzene Heating;	71%

2,3-dibromopropanal (5221-17-0) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2-(1,2-dibromoethyl)-5,5-dimethyl-1,3-dioxane

Conditions	Yield
With cationite KU-2-8 In benzene Heating;	64%

diazomethane (186581-53-3, 908094-01-9) + diethyl ether (60-29-7) + 2,3-dibromopropanal (5221-17-0) → 3,4-dibromobutan-2-one (25109-57-3)

diazomethane (186581-53-3, 908094-01-9) + 2,3-dibromopropanal (5221-17-0) → 3,4-dibromobutan-2-one (25109-57-3)

Conditions	Yield
With diethyl ether

1,4-dioxane (123-91-1) + 2,3-dibromopropanal (5221-17-0) + N-methyl-p-aminobenzoic acid (10541-83-0) → 6-carboxy-1-methyl-quinolinium; bromide

1,4-dioxane (123-91-1) + 2,3-dibromopropanal (5221-17-0) + 4-(benzyl-methyl-amino)-benzoic acid (25070-91-1) → 6-carboxy-1-methyl-quinolinium; bromide

pyridine (110-86-1) + 2,3-dibromopropanal (5221-17-0) → 1-(2-amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-pyridinium; iodide

Conditions	Yield
und Behandeln des erhaltenen Reaktionsprodukts mit 2,5,6-Triamino-3H-pyrimidin-4-on und KI;

methanol (67-56-1) + 2,3-dibromopropanal (5221-17-0) + formimidomethylester hydrochloride (15755-09-6) → 1,2-dibromo-3,3-dimethoxypropane (248955-54-6)

4,5,6-triamino-1H-pyrimidine-2-thione (1073-99-0) + 2,3-dibromopropanal (5221-17-0) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1) → N-{4-[(4-amino-2-thioxo-1,2-dihydro-pteridin-6-ylmethyl)-amino]-benzoyl}-L-glutamic acid (103207-69-8)

4,5,6-triamino-1H-pyrimidine-2-thione (1073-99-0) + 2,3-dibromopropanal (5221-17-0) + 4-amino-benzoic acid (150-13-0) → 4-[(4-amino-2-thioxo-1,2-dihydro-pteridin-6-ylmethyl)-amino]-benzoic acid (92253-82-2)

5,6-diaminouracil (3240-72-0) + 2,3-dibromopropanal (5221-17-0) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1) → N-{4-[(2,4-dioxo-1,2,3,4-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoyl}-L-glutamic acid (25663-25-6)

Conditions	Yield
With sodium acetate; acetic acid

N-(4-aminobenzoyl)-B-alanine (7377-08-4) + 2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) → N-pteroyl-β-alanine (15677-93-7)

Conditions	Yield
With sodium dichromate
With iodine

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + N-methyl-p-aminobenzoic acid (10541-83-0) → 10-methyl-pteroic acid (5623-18-7)

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + 4-(N-butylamino)benzoic acid (4740-24-3) → 10-butyl-pteroic acid

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + N-(4-amino-benzoyl)-alanine (99146-89-1) → N-pteroyl-DL-alanine

Conditions	Yield
With sodium dichromate
With iodine

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + p-(N-methylamino)benzoyl-L-glutamic acid (52980-68-4) → N10-methylfolic acid (2410-93-7)

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + N-(4-amino-3-methyl-benzoyl)-L-glutamic acid (875430-61-8) → N-(3'-methyl-pteroyl)-L-glutamic acid

N-(4-aminobenzoyl)-glutamic acid (4230-33-5) + 2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) → folate (65165-92-6)

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + (4-amino-benzoylamino)-malonic acid → pteroylamino-malonic acid

Conditions	Yield
With iodine
With sodium dichromate

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + 4-amino-benzoic acid (150-13-0) → pteroic acid (119-24-4)

Conditions	Yield
With ethanol Loesung vom pH 4;

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 2,3-dibromopropanal (5221-17-0) + o-toluidine (95-53-4) → 2-amino-6-o-toluidinomethyl-3H-pteridin-4-one

Conditions	Yield
With sodium dichromate

p-aminophenylarsonic acid (98-50-0) + 2,4,5,6-tetraaminopyrimidine (1004-74-6) + 2,3-dibromopropanal (5221-17-0) → {4-[(2,4-diamino-pteridin-6-ylmethyl)-amino]-phenyl}-arsonic acid (109160-53-4)

Conditions	Yield
With hydrogenchloride; sodium dichromate; acetic acid pH 3-4;

2,4,5,6-tetraaminopyrimidine (1004-74-6) + 2,3-dibromopropanal (5221-17-0) + N-(4-amino-benzoyl)-serine (879278-42-9) → N-{4-[(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoyl}-DL-serine

Conditions	Yield
With water; iodine

N-(4-aminobenzoyl)-glutamic acid (4230-33-5) + 2-methylsulfanyl-pyrimidine-4,5,6-triamine (1431-40-9) + 2,3-dibromopropanal (5221-17-0) → N-{4-[(4-amino-2-methylsulfanyl-pteridin-6-ylmethyl)-amino]-benzoyl}-DL-glutamic acid (94543-82-5)

Conditions	Yield
With sodium acetate

Upstream product

• 10463-48-6 3,4-dibromo-1-butene 
• 18791-02-1 2,3-dibromo-propionyl chloride 
• 627-15-6 1,3-dibromopropene 
• 85858-56-6 4,5-dibromo-pent-2-enoic acid 
• 67-66-3 chloroform 
• 7732-18-5 water 
• 10028-15-6 ozone 
• 107-02-8 acrolein 
• 109-64-8 1,3-dibromo-propane 

Downstream Products

• 7726-95-6 bromine 
• 56-82-6 Glyceraldehyde 
• 869496-63-9 C₁₀H₅Cl₂NO₂ 
• 933709-27-4 3-(4-methoxyphenyl)isoxazole-5-carbaldehyde 
• 72418-40-7 3-phenylisoxazole-5-carbaldehyde 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 10035-10-6 hydrogen bromide 
• 57-48-7 fructose 
• 57-48-7 sorbose 
• 600-05-5 2,3-dibromopropionic acid 
• 14925-39-4 2-bromoacrolein 
• 97115-74-7 N-{4-[(2-amino-4-dimethylamino-pteridin-6-ylmethyl)-methyl-amino]-benzoyl}-L-glutamic acid 
• 578-12-1 2'-fluorofolic acid 
• 103508-85-6 N-{4-[(2-amino-4-dimethylamino-pteridin-6-ylmethyl)-amino]-benzoyl}-L-glutamic acid 

Relevant articles and documents

Enantioselective synthesis of trans-fused bicyclo[5.3.0]decane systems via a tandem [4+3] cycloaddition-Nicholas reaction

An enantioselective synthetic methodology to prepare trans-fused bicyclo[5.3.0]decane systems is presented. It is a very versatile methodology based on two key reactions: [4+3] cycloaddition reaction (to generate the seven-membered ring) and the Nicholas reaction (that facilitates the insertion of the five-membered ring). This methodology allows the easy preparation of a wide range of bioactive natural products containing the transfused bicyclo[5.3.0]decane system. The application of this methodology to the enantioselective synthetic approach to the pseudoguaiane carbon- skeleton is described.

Method for synthesizing bis(2-methyl-3-furyl) disulfide

The invention relates to a method for synthesizing bis(2-methyl-3-furyl) disulfide. The method comprises the following steps: (1) enabling acrolein to react with bromine to obtain a product 1; (2) adding the product 1 into an absolute ethyl alcohol solution of sodium hydroxide to prepare propiolaldehyde diethyl acetal; (3) enabling ethyl ether and bromoethane to react with chloroethane in presence of magnesium, then adding mixed liquid of the propiolaldehyde diethyl acetal and the ethyl ether and subsequently adding mixed liquid of acetaldehyde and ethyl ether for carrying out a reaction, and hydrolyzing to prepare 4-hydroxy-2-pentyne propanal diethyl acetal; (4) adding the 4-hydroxy-2-pentyne propanal diethyl acetal into a water solution containing sulfuric acid, pentane and potassium thiocyanate to prepare a product 4; (5) adding the product 4 into a sodium hydroxide water solution to prepare the bis(2-methyl-3-furyl) disulfide. Compared with the existing synthesis method, the method provided by the invention is easy in control of reaction conditions, fewer in side reactions, easy in control of intermediate products and higher in yield of a target product, thus having wide application prospect.

Propynal equivalents and diazopropyne: Synthesis of all mono-13C isotopomers

Mechanistic and spectroscopic investigations of reactive C 3H2 hydrocarbons necessitated the preparation of diazopropyne isotopomers bearing mono-13C substitution at each of the three unique positions. The diazo compounds and their tosylhydrazone precursors were prepared from the mono-13C isotopomers of propynal (in the form of either the aldehyde or the diethyl acetal). The introduction of 13C-labeling at either alkyne position in propynal utilized the Corey - Fuchs procedure for chain homologation.