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Acros Organics & Maybridge - D

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Diphenylphosphinyl chloride<br />

APPLICATION GUIDE<br />

Coupling Chemistry<br />

* Coupling agent Used for the activation of acids via in situ formation of the diphenylphosphinic mixed<br />

anhydrides. Used in peptide chemistry. These mixed anhydrides react with amines (primary amines<br />

give better yields than secondary amines) to give amides and with thiols to give thiol esters.<br />

Recommended for the preparation of amides from acrylic acids. JCS(P1) 1985, 461; S 1980, 385<br />

Organometallic Chemistry<br />

* Acid to ketone Acids are converted to ketones via activation to the mixed anhydride, followed by<br />

reaction with organometallic reagents such as ethylmagnesium bromide. CC 1986, 412<br />

Protecting Group Chemistry<br />

* Protection of amines Used for the N-protection of amino esters (N-methylmorpholine, DCM). DPP<br />

protecting group is slightly more acid labile than the BOC protecting group. JCS(P1) 1984, 1357<br />

Diphenylphosphinyl chloride, 98%<br />

<strong>Acros</strong> <strong>Organics</strong> Product code Packaging Pack size Price<br />

212960100 Glass bottle 10 g INR 1,680<br />

212960500 Glass bottle 50 g INR 6,650<br />

R10 R34<br />

S16 S26 S36/37/39<br />

S45<br />

Moisture sensitive<br />

C 12 H 10 ClOP (C 6 H 5 ) 2 P(O)Cl<br />

CAS: 1499-21-4<br />

MFCD00002077<br />

FW: 236.64<br />

bp: 222 °C (16 mmHg)<br />

Fp: 26 °C<br />

d: 1.240<br />

Diphenyl phosphite<br />

contains varying amounts of phenol and (C6H5O)3P<br />

Diphenyl phosphorochloridate , see Diphenyl chlorophosphate on page 924<br />

n 20<br />

D : 1.608 -1.612<br />

<strong>Acros</strong> <strong>Organics</strong> Product code Packaging Pack size Price<br />

117390050 Glass bottle 5 g INR 1,260<br />

117395000 Glass bottle 500 g INR 3,000<br />

117390010 Glass bottle 1 kg INR 5,430<br />

R34<br />

S26 S36/37/39 S45<br />

Moisture sensitive<br />

C 12 H 11 O 3 P (C 6 H 5 O) 2 P(O)H<br />

CAS: 4712-55-4<br />

MFCD00044497<br />

FW: 234.19<br />

mp: 12 °C<br />

bp: 218-219 °C (26<br />

mmHg)<br />

Fp: 176 °C<br />

d: 1.217<br />

n 20<br />

D : 1.5565 -1.5585<br />

Diphenylphosphoryl azide<br />

APPLICATION GUIDE<br />

Coupling Chemistry<br />

* Peptide synthesis N-Protected amino acids are converted to acyl azides, which undergo Curtius<br />

rearrangement and applied in peptide synthesis. JACS 1972, 94, 6203<br />

Decarbonylation<br />

* Decarbonylation Decarbonylation of primary aldehydes occurs at RT in the presence of catalytic<br />

chlorotris(triphenylphosphine)rhodium(I). Minimal formation of alkene by-product. JOC 1992, 57,<br />

5075<br />

Interconversion of functional groups<br />

* Carboxylic acid to ester An ester is formed in the presence of an alcohol, when no alcohol is added,<br />

the isocyanate is isolated as the product of Curtius rearrangement. CR 1948, 43, 203<br />

Lactonisation, lactamisation<br />

* Macrocyclic lactams Dicarboxylic acids, when activated can condense with diamines to form<br />

lactams. TL 1990, 31, 6469<br />

Oxidation<br />

* Ketone to carboxylic acid Aryl carboxylic acids are obtained from alkyl aryl ketones with the process<br />

proceeding via an enamine intermediate. JOC 1978, 43, 2936<br />

http://www.acros.com Diphenylphos<br />

Diphenylphosphoryl azide, 98%<br />

<strong>Acros</strong> <strong>Organics</strong> Product code Packaging Pack size Price<br />

409040250 Glass bottle 25 g INR 2,410<br />

409041000 Glass bottle 100 g INR 5,860<br />

409045000 Glass bottle 500 g INR 23,130<br />

R23/24/25 R36/37/<br />

38<br />

S26 S36/37/39 S45<br />

Store below +4ºC<br />

C12H10N3O3P CAS: 26386-88-9<br />

MFCD00001987<br />

FW: 275.19<br />

bp: 157 °C (0.2 mmHg)<br />

Fp: 112 °C<br />

d: 1.273<br />

n 20<br />

D : 1.55 -1.552<br />

Diphenyl phthalate, 98%<br />

<strong>Acros</strong> <strong>Organics</strong> Product code Packaging Pack size Price<br />

325070250 Glass bottle 25 g INR 730<br />

R36/37/38<br />

S26 S37/39<br />

C 20 H 14 O 4<br />

CAS: 84-62-8<br />

MFCD00003038<br />

FW: 318.32<br />

mp: 72-76 °C<br />

4,4-Diphenylpiperidine hydrochloride, 95+%<br />

<strong>Maybridge</strong> Product code Packaging Pack size Price<br />

MAY00206DE Glass bottle 5 g INR 20,600<br />

R36/37/38<br />

S22 S26 S36/37/39<br />

C17H19N.ClH CAS: 63675-71-8<br />

MFCD01700799<br />

FW: 273.80<br />

,-Diphenyl-4-piperidinomethanol, 98+%<br />

<strong>Acros</strong> <strong>Organics</strong> Product code Packaging Pack size Price<br />

232520050 Glass bottle 5 g INR 1,600<br />

232520250 Glass bottle 25 g INR 4,480<br />

R36/37/38<br />

S24/25<br />

C18H21NO CAS: 115-46-8<br />

MFCD00066980<br />

FW: 267.36<br />

mp: 160-163 °C<br />

Please enquire for bulk quantities 931<br />

O<br />

O<br />

P N<br />

O<br />

NH<br />

N +<br />

N<br />

HN OH<br />

ClH<br />

D

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