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5754-34-7

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5754-34-7 Usage

Description

4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE, also known as 2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethanol, is an organic compound with a unique structure that features a dioxolane ring and a hydroxyethyl group. This chemical structure endows it with specific properties that make it suitable for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is used as a key component in the preparation of cationic lipids and stealth lipids for the treatment of a variety of disorders. Its unique structure allows for the formation of stable and biocompatible lipid-based drug delivery systems, which can enhance the solubility, bioavailability, and targeted delivery of therapeutic agents.
Used in Cosmetics Industry:
In the cosmetics industry, 4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is used as an ingredient in the formulation of various skincare and hair care products. Its ability to form stable emulsions and its compatibility with other ingredients make it a valuable component in creating effective and aesthetically pleasing cosmetic formulations.
Used in Chemical Synthesis:
4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE is also utilized as an intermediate in the synthesis of various chemical compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its versatile structure and reactivity make it a valuable building block for the development of new and innovative products.

Check Digit Verification of cas no

The CAS Registry Mumber 5754-34-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,5 and 4 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5754-34:
(6*5)+(5*7)+(4*5)+(3*4)+(2*3)+(1*4)=107
107 % 10 = 7
So 5754-34-7 is a valid CAS Registry Number.
InChI:InChI=1/C27H28ClNO5/c1-5-34-27(31)24-15(2)29-20-12-18(16-6-9-19(28)10-7-16)13-21(30)26(20)25(24)17-8-11-22(32-3)23(14-17)33-4/h6-11,14,18,25,29H,5,12-13H2,1-4H3

5754-34-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

1.2 Other means of identification

Product number -
Other names rac-1,2-O-isopropylidenebutane-1,2,4-triol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5754-34-7 SDS

5754-34-7Synthetic route

D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

acetone
67-64-1

acetone

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 4h;98%
With toluene-4-sulfonic acid at 20℃; for 20h;97%
With toluene-4-sulfonic acid86%
4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane
167629-45-0

4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water90%
D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With camphor-10-sulfonic acid85%
With camphor-10-sulfonic acid In acetonitrile at 20℃;80%
Stage #1: D,L-1,2,4-butanetriol; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20℃; for 4h; Reflux;
Stage #2: In methanol at 0℃; for 12h;
74%
methylene chloride (CH2 Cl2)

methylene chloride (CH2 Cl2)

para-toluene sulfonic acid (p-TsOH)

para-toluene sulfonic acid (p-TsOH)

D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With magnesium sulfate In methanol; water; acetone75%
tert-butyl-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-dimethyl-silane

tert-butyl-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-dimethyl-silane

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.25h;72%
D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

2-Methoxypropene
116-11-0

2-Methoxypropene

A

(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol
56476-33-6

(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol

B

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

C

2-(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)-2-methoxypropane

2-(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)-2-methoxypropane

D

2-(2,2-dimethyl-1,3-dioxan-4-ylmethoxy)-2-methoxypropane

2-(2,2-dimethyl-1,3-dioxan-4-ylmethoxy)-2-methoxypropane

E

2,2-bis(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)propane

2,2-bis(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)propane

Conditions
ConditionsYield
With butyltin(IV) chloride dihydroxide for 90h; Product distribution; Ambient temperature; var. of reagent, ratio, time, further with 2,2-dimethoxypropane;A 3.0 g
B 13.3 g
C n/a
D n/a
E 0.4 g
2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde
83141-42-8

2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
reduction;
D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

acetone
67-64-1

acetone

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid
D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

acetone
67-64-1

acetone

A

(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol
56476-33-6

(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol

B

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
toluene-4-sulfonic acid Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With toluene-4-sulfonic acid Yield given. Yields of byproduct given. Title compound not separated from byproducts;
D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

A

(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol
56476-33-6

(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol

B

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In acetone at 20℃; for 0.5h;
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate
76099-47-3

2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;100%
With triethylamine In toluene at 20℃; for 4h; mesylation;94%
With triethylamine In dichloromethane at 0℃; for 1.5h;91%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate
55559-75-6

2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane 1) 0-5 deg C, 3.5 h; 2) rt, 6 h;99%
With pyridine 1.) 0 deg C, 2 h, 2.) -20 deg C, overnight;87%
With pyridine at 0 - 20℃; for 24h;81%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

allyl bromide
106-95-6

allyl bromide

(±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

(±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;98%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde
83141-42-8

2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane Ambient temperature;93%
With aluminum oxide; pyridinium chlorochromate In dichloromethane at 0 - 20℃;75%
With camphor-10-sulfonic acid; pyridinium chlorochromate In dichloromethane for 3h;74%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

benzyl bromide
100-39-0

benzyl bromide

(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane
94426-71-8

(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;91%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide for 3h; Ambient temperature;71%
With sodium hydride 1.) DMF, RT, 0.5 h, 2.) 30 deg C, 1.5 h; Yield given. Multistep reaction;
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

O-(4-methoxybenzyl)-trichloroacetimidate
89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane
167629-45-0

4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane91%
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 12h;91%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

(±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

(±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With sodium hydroxide In toluene at 30℃; for 6h;90%
With sodium hydroxide at 30℃; for 2h;
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

oleoyl chloride

oleoyl chloride

(Z)-Octadec-10-enoic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

(Z)-Octadec-10-enoic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Conditions
ConditionsYield
With dmap; TEA for 6h; Ambient temperature;88%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

2,2-dimethyl-4-[2-(tetrahydro-furan-2-yloxy)-ethyl]-[1,3]dioxolane

2,2-dimethyl-4-[2-(tetrahydro-furan-2-yloxy)-ethyl]-[1,3]dioxolane

Conditions
ConditionsYield
With indium(III) chloride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 3h;87%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 12h;75%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

4-(dimethylamino)benzenesulfonyl chloride
19715-49-2

4-(dimethylamino)benzenesulfonyl chloride

rac-O-isopropylidene-3,4-dihydroxybutyl p-dimethylaminobenzenesulfonate

rac-O-isopropylidene-3,4-dihydroxybutyl p-dimethylaminobenzenesulfonate

Conditions
ConditionsYield
With pyridine at 4℃; for 72h; Tosylation;86%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

4-(2-methanesulfonylethyl)-2,2-dimethyl-1,3-dioxolane

4-(2-methanesulfonylethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With triethylamine In dichloromethane at -5℃; for 2.5h; Inert atmosphere;84.1%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate
76099-47-3

2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -5℃; for 2.5h; Inert atmosphere;84.1%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

2-(phenylsulfonyl)tetrahydro-2H-pyran
96754-03-9

2-(phenylsulfonyl)tetrahydro-2H-pyran

2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tetrahydro-pyran
120346-89-6

2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tetrahydro-pyran

Conditions
ConditionsYield
With sodium hydrogencarbonate; magnesium bromide In tetrahydrofuran Ambient temperature; overnight (15-24 hrs);78%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

N-3-benzoylthymine
4330-20-5

N-3-benzoylthymine

(RS)-1-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethyl]thymine
471256-49-2

(RS)-1-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethyl]thymine

Conditions
ConditionsYield
With polystyrene-triphenylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu condensation;67%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

3,3-dichloro-1,1,1,2,2-pentafluoropropane
422-56-0

3,3-dichloro-1,1,1,2,2-pentafluoropropane

1,3-dichloro-1,1,2,2,3-pentafluoropropane
507-55-1

1,3-dichloro-1,1,2,2,3-pentafluoropropane

perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride
2641-34-1

perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride

C16H13O6F17

C16H13O6F17

Conditions
ConditionsYield
With sodium fluoride at 20℃; for 20h;67%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

4-chloro-2,3-dimethylpyridine-N-oxide
59886-90-7

4-chloro-2,3-dimethylpyridine-N-oxide

4-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-2,3-dimethylpyridine 1-oxide
1020733-19-0

4-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-2,3-dimethylpyridine 1-oxide

Conditions
ConditionsYield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 4-chloro-2,3-dimethylpyridine-N-oxide In dimethyl sulfoxide at 60℃; for 2h;
63.8%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate
35717-98-7

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate

[2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethoxymethyl]-phosphonic acid diisopropyl ester
918795-56-9

[2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethoxymethyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 16h;59%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline
765962-75-2

3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

3-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline
1084333-27-6

3-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

Conditions
ConditionsYield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In tetrahydrofuran for 0.166667h;
Stage #2: 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline In tetrahydrofuran for 0.5h;
59%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Methacryloyl chloride
920-46-7

Methacryloyl chloride

2-(2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methacrylate

2-(2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methacrylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;58.4%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

(+/-)-1,2-O-isopropylydene-4-(2,4-dinitrophenyloxy)-1,2-butanediol
40742-25-4

(+/-)-1,2-O-isopropylydene-4-(2,4-dinitrophenyloxy)-1,2-butanediol

Conditions
ConditionsYield
With triethylamine at 25℃; for 6h;58%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane
98095-37-5

4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With 1H-imidazole; iodine; triphenylphosphine at 0 - 20℃; Darkness;49%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.666667h; Sealed tube; Inert atmosphere;44%
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2
2: NaI; K2CO3
View Scheme
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

isopropylidene ketal of rac-3,4-dihydroxybutyl bromide
89942-18-7

isopropylidene ketal of rac-3,4-dihydroxybutyl bromide

Conditions
ConditionsYield
With bromine; triphenylphosphine In N,N-dimethyl-formamide for 1h; Ambient temperature;48%
With Bromoform; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 20h;47.8%
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2.5 h / -5 °C / Inert atmosphere
2: magnesium bromide ethyl etherate / diethyl ether / Inert atmosphere
View Scheme
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

piperidinophosphoramidic dichloride

piperidinophosphoramidic dichloride

[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl] piperidinophosphoramidate

[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl] piperidinophosphoramidate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran43%
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
5754-34-7

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

2-fluro-4-iodoaniline
29632-74-4

2-fluro-4-iodoaniline

2,4,6-trifluorobenzonitrile
96606-37-0

2,4,6-trifluorobenzonitrile

2-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-4-fluoro-6-[(2-fluoro-4-iodophenyl)amino]benzonitrile
1084333-29-8

2-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-4-fluoro-6-[(2-fluoro-4-iodophenyl)amino]benzonitrile

Conditions
ConditionsYield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane; 2,4,6-trifluorobenzonitrile With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 2-fluro-4-iodoaniline With potassium tert-butylate at 20℃; for 3h;
32%

5754-34-7Relevant articles and documents

Studies on the cholinergic receptor. 6. Synthesis and muscarinic activity of 2-methyl-4-(2-dimethylaminoethyl)-1,3-dioxolane methiodide.

Chang,Ridley,Triggle

, p. 1237 - 1237 (1971)

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iPF2α-III-17,18,19,20-d4: Total synthesis and metabolism

Kim, Seongjin,Powell, William S.,Lawson, John A.,Jacobo, Sheila H.,Pratico, Domenico,FitzGerald, Garret A.,Maxey, Kirk,Rokach, Joshua

, p. 1613 - 1617 (2005)

The first total synthesis of 17,18,19,20-d4-iPF 2α-III 32, a deuterated analog of iPF2α-III, is described. We have used this analog in some β-oxidation studies with rat liver homogenates and have shown that 32 was metabolized to 17,18,19,20-tetradeutero-2,3-dinor-iPF2α-III 36 and 17,18,19,20-tetradeutero-2,3-dinor-5,6-dihydro-iPF2α-III 37.

Condensation of 1,2,4-Butanetriol with Carbonyl Compounds and Reactions of Hydroxyalkyl-1,3-dioxacyclanes

Raskil’dina,Borisova, Yu. G.,Zlotskii

, p. 1601 - 1605 (2018/11/10)

A mixture of isomers of 2-(1,3-dioxolan-4-yl)ethanol and 1,3-dioxan-4-ylmethanol was prepared by reaction of 1,2,4-butanetriol with paraformaldehyde. This mixture was subjected to O-alkylation, O-acylation, condensation with phenyl isocyanate, and substitution of OH groups for Cl. The relative activity of acetone derivatives of glycerol and 1,2,4-butanetriol in reactions with allyl chloride and benzyl chloride was estimated.

Identification of a Water-Soluble Indirubin Derivative as Potent Inhibitor of Insulin-like Growth Factor 1 Receptor through Structural Modification of the Parent Natural Molecule

Cheng, Xinlai,Merz, Karl-Heinz,Vatter, Sandra,Zeller, Jochen,Muehlbeyer, Stephan,Thommet, Andrea,Christ, Jochen,W?lfl, Stefan,Eisenbrand, Gerhard

supporting information, p. 4949 - 4962 (2017/06/28)

Indirubins have been identified as potent ATP-competitive protein kinase inhibitors. Structural modifications in the 5-and 3′-position have been extensively investigated, but the impact of substituents in 5′-position is not equally well-studied. Here, we report the synthesis of new indirubin 3′-and 5′-derivatives in the search of water-soluble indirubins by introducing basic centers. Antiproliferative activity of all compounds in tumor cells was evaluated along with kinase inhibition of selected compounds. The results show the 3′-position to tolerate large substituents without compromising activity, whereas bulk and rigid substituents in 5′-position appear unfavorable. Screening molecular targets of water-soluble 3′-oxime ethers revealed 6ha as preferential inhibitor of insulin-like growth factor 1 receptor (IGF-1R) in a panel of 22 protein kinases and in cells. Consistently, 6ha inhibited tumor cell growth in the NCI 60 cell line panel and induced apoptosis. The results indicate that the 5′-position provides limited space for chemical modifications and identify 6ha as a potent water-soluble indirubin-based IGF-1R inhibitor.

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